Iodobenzene-catalyzed alpha-acetoxylation of ketones. in situ generation of hypervalent (diacyloxyiodo)benzenes using m-chloroperbenzoic acid.

doi:10.1021/JA0542800

Paper

Iodobenzene-catalyzed alpha-acetoxylation of ketones. in situ generation of hypervalent (diacyloxyiodo)benzenes using m-chloroperbenzoic acid.

Published Aug 16, 2005 · M. Ochiai, Yasunori Takeuchi, Tomoko Katayama

Journal of the American Chemical Society

283

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Abstract

Reported here for the first time is the iodobenzene-catalyzed alpha-oxidation of ketones, in which diacyloxy(phenyl)-lambda3-iodanes generated in situ act as real oxidants of ketones and m-chloroperbenzoic acid serves as a terminal oxidant. Oxidation of a ketone with m-chloroperbenzoic acid in acetic acid in the presence of a catalytic amount of iodobenzene, BF3.Et2O, and water at room temperature under argon affords an alpha-acetoxy ketone in good yield. p-Methyl- and p-chloroiodobenzene also serve as efficient catalysts in this direct oxidation. We found that when the reaction was carried out in the absence of a catalytic amount of iodobenzene, Baeyer-Villiger oxidation of a ketone took place. It is noted that use of water and BF3.Et2O is crucial to the success of this alpha-acetoxylation.

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Study Snapshot

Iodobenzene-catalyzed alpha-acetoxylation of ketones, using m-chloroperbenzoic acid and BF3.Et2O, can efficiently generate hypervalent (diacyloxyiodo)benzenes, offering potential applications in

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Iodobenzene-catalyzed alpha-acetoxylation of ketones. in situ generation of hypervalent (diacyloxyiodo)benzenes using m-chloroperbenzoic acid.

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